The present invention relates to novel compositions and, more particularly, to a class of compounds having specific quaternized amine based upon a castor amido amine linked to specific phosphate esters. Castor is an oil that contains a high quantity of a hydroxy containing C-18 having unsaturation present in the group. This allows for the synthesis of a phospholipid composition, which has outstanding emulsification properties and is liquid and surprisingly water-soluble. In addition this material is not toxic to human skin and is well tolerated by human tissue making it suitable for use in the preparation products for personal care applications.
Phosphate ester and quaternary amine compounds are well known and have been widely used for many years. More recently, various betaine-type derivatives having, in general, quaternized alkyl amine groups and at least one phosphorous-containing anion in the molecule referred to hereinafter as xe2x80x9csynthetic phospholipidsxe2x80x9d, have been disclosed. The U.S. Pat. Nos. are 3,856,893 and 3,928,509 to Diery et al. Diery discloses that the phosphonate compounds of his invention are active anti-microbial compounds. Later amdido amine and imidazoline derivatives were disclosed for example, in U.S. Pat. Nos. 4,215,064; 4,233,192 and 4,380,637 to Lindemann et al., U.S. Pat. Nos. 4,209,449; 4,336,385 and 4,503,002 to Mayhew et al., and U.S. Pat. Nos. 4,243,602; 4,283,542 and 4,336,386 to O""enick et al. These synthetic phospholipids are suggested as exhibiting an outstanding combination of surfactant characteristics as well as being well tolerated by human tissue, i.e., they exhibit exceptionally low ocular irritation and oral toxicity. While these known phospholipids have been found useful as surfactants in a variety of personal care, they have not exhibited an ability to protect the skin from irritation or provide barrier properties to the skin, protecting it from the negative effects of chemicals and environmental effects.
It is very desirable to provide a material from aqueous solution that will protect the skin from environmental irritants such as ozone, and other pollutants. The compounds of the present invention can be formulated into body washes and other skin products and protect the skin from damage. In addition the di-nature of the compounds provides for outstanding substantivity and the phospholipid nature of the molecule allow for very mild natural like materials that can be used in products where low irritation is important.
Objective of the Invention
It is the objective of the invention to provide a novel castor based phospholipid and a process of its use which comprises using it as an emulsifier and conditioner in personal care applications.
In accordance with the present invention we have now been discovered novel phospholipid compound, which conform to the following structure: 
wherein;
R is ricinoleic.
The present invention is directed toward a process for conditioning skin that comprises contacting the skin with an effective conditioning amount of a phospholipid compound, which conforms to the following structure: 
wherein;
R is the ricinoleic moiety conforming to the following structure
xe2x80x94(CH2)7xe2x80x94CHxe2x95x90CHxe2x80x94CH2CH(OH)(CH2)5CH3.
The effective conditioning concentration ranges from 0.1% to 15% by weight of the phospholipid. In a preferred embodiment the effective conditioning concentration ranges from 1.0% to 5% by weight of the phospholipid.
Preferred Embodiments
In a preferred embodiment the effective emulsifying concentration ranges from 0.5% to 25% by weight with 3 to 15% being the preferred concentration.
In another preferred embodiment the emulsions contain an anionic surfactant selected from the group consisting of alcohol sulfates. Alcohol ether sulfates and alpha olefin sulfonate.
In still another preferred embodiment the emulsions contain a non-ionic surfactant selected from the group consisting of alkanolamids, and fatty alcohol ethoxylated.
The present invention is directed to novel phospholipid compounds, which conform to the following structure: 
wherein;
R is ricinoleic which is xe2x80x94(CH2)7xe2x80x94CHxe2x95x90CHxe2x80x94CH2CH(OH)(CH2)5CH3.
The compounds of the present invention are prepared by reacting first reacting castor with dimethylaminopropyl amine (DMAPA) to give a tertiary amine intermediate. 
Ricinoleylamido-amine
This intermediate is then reacted with 3-chloro-2hydroxypropyl-phosphate made in accordance with the procedure outlined in U.S. Pat. No. 4,283,542 to O""Lenick, incorporated herein by reference. 
wherein;
R is ricinoleic.
The compounds of the present invention are made reaction of the intermediate above with the dimmer diamido-amine under aqueous conditions. The product of the invention is thereby attained.
The compatibility of this novel phospholipid compounds of the invention with human tissue, i.e., dermal and eye tissue has also been tested. In these tests, 48-hour human patch dermal evaluations (5% in water), in vitro ocular evaluations (3% in water) and repeated insult patch tests (3% in water) determined that the compounds are substantially non-irritating to humans, they are safe and suitable for use in eye area products and are not a skin sensitizer to humans.